From 1991 to 2003, Matthews predominantly focused on songwriting and performing with the Dave Matthews Band, which he started in Charlottesville, Virginia in 1991. Since then, he has also done various solo performances and produced other records. During the period from 2000 to 2010, his band sold more tickets and earned more money than any other act in North America.[4] The band's 2012 album Away from the World made them the only group to have six consecutive studio albums debut at number one on the Billboard charts.

In 1974, the Matthews family moved to Cambridge, England for a year before returning to New York, where his father died from lung cancer in 1977. Biographer Nevin Martell argues that Dave's father's death may be an impetus for his "carpe diem" lyrics.[8] At some point while residing in New York, Matthews attended his first concert, when his mother took him to a performance by Pete Seeger.[9] The family returned to Johannesburg in 1977.[10]

Matthews moved to New York in 1986 where he worked for IBM for a short time,[10] then joined his mother that same year in Charlottesville, Virginia, a town Matthews' family had lived in before he was born.[10] In Charlottesville, he became part of the local music community. Pursuing various interests, Matthews acted in various local productions.[citation needed] Although Matthews had started playing the guitar at age nine, it was only in Charlottesville that he started performing publicly.[10] Through a mutual friend, Nic Cappon, Matthews met local star (and future collaborator) Tim Reynolds. In time, Reynolds had Matthews join him on stage, and eventually Matthews was persuaded to record some of his own songs.[10][13] This led to his first professional musical gig at a modern dance performance by the Miki Liszt Dance Company, based at McGuffey Art Center in Charlottesville, singing "Meaningful Love", composed by John D'earth and Dawn Thompson.[14] In 1991, he hatched the idea to form his own band.[10] Prior to recording his first demo, Matthews bartended at Miller's in Charlottesville.[15]

In early 1994, Matthews' older sister, Anne, who lived in South Africa, was murdered by her husband, who subsequently committed suicide, on or around January 27 of that year.[17] The event had a profound effect on Matthews' outlook on life and was referenced in a few of his songs. On January 29, 1994, he performed with Tim Reynolds at The Wetlands in New York, where he dedicated that performance "to her [Anne's] memory". Dave Matthews Band's Under the Table and Dreaming, released later that year, was dedicated to her.[17] Anne Matthews was survived by her two children who, upon her death, traveled to America, where Dave and his younger sister, Jane, took responsibility for their upbringing (his sister is the namesake of DMB's song, "The Song That Jane Likes").[17]

L to R: Reynolds and Matthews in 2007 performing in Amherst, MA in one of many acoustic shows the two play as a duo.

Matthews focused primarily on songwriting and performances with the Dave Matthews Band from 1990 to 2003. DMB is an artistic blend of acoustic guitar, bass, sax, drums and fiddle music. In 1994, DMB signed with RCA Records.[15][18] Since that period, he has occasionally ventured outside the band in various solo performances and records.
Matthews sang on the track "Sing Along" on Blue Man Group's second album The Complex in 2003.[19] Later that year he released a solo album, "Some Devil", which went platinum; its single, "Gravedigger", won a Grammy Award in 2004.[20] To support the album, Matthews toured with a group of musicians (many of whom performed on "Some Devil") under the name Dave Matthews & Friends.[21][22]

In 2007, Matthews guest starred in the Fox medical-drama series House in the episode "Half-Wit". He played a piano-playing musical savant who ended up having the two hemispheres of his brain severed from each other in order to recover from his epilepsy, but at the expense of his musical abilities. Dave had a piano double for the complex pieces, but played the simpler pieces himself.[31] In the season one episode of House, "Love Hurts", the song "Some Devil" can be heard playing at the end. In another episode, one of the tracks from Stand Up, "You Might Die Trying" was played in the season five episode, "Not Cancer".[32]

The fifth time Matthews appeared as musical guest on Saturday Night Live in November 2009 (which was also the fourth time the Dave Matthews Band appeared on the show), he made an appearance as Ozzy Osbourne in a skit called "The Mellow Show." Bill Hader impersonated Matthews in the same skit.

In 1999, Matthews purchased more than ten acres of land in Albemarle County, Virginia, known as Blenheim Farm, to preserve its historical significance. He later decided to plant grapes on the property, since it is located within both the Virginia and Monticelloviticultural areas. Blenheim Vineyards was founded in 2000, and currently produces 5,500 cases of wine per year, including their signature Petit Verdot and several special edition wines which have featured unique labels with drawings by Matthews himself.[34]

In April 2012, Matthews was credited as producer on a documentary, "Last Call at the Oasis", directed by Jessica Yu.[38]

In early 2013, Matthews participated in a jam session at Blade Studios in Shreveport, Louisiana with Jakob Dylan, Charlie Sexton, Blade studios co-owner Brady Blade, and Sexton's brother Will. This eventually led to the formation of a band called The Nauts with Matthews, Dylan, Blade, and the Sexton brothers as members. However, there has been no news regarding an album release since that jam session.[39]

Dave Matthews married longtime girlfriend Ashley Harper in 2000. They have twin daughters, Stella Busina and Grace Anne, born August 15, 2001, and a son, August Oliver, born June 19, 2007. They reside in Seattle, Washington & have a vacation home located in Mechanicville, New York.[40] In a 2001 interview, Matthews stated that he was agnostic.[41] Matthews is also on the Farm Aid board of directors along with fellow musicians Willie Nelson, John Mellencamp and Neil Young, who raise money for family farmers in the United States.[42]

Dave Matthews has donated generously to liberal causes and is a Democrat.

Matthews published an Internet video prior to the 2000 U.S. Presidential election, urging viewers to vote without advocating any candidate. He mentioned only Ralph Nader by name, and updated fans about the recording sessions for Everyday. Although his music often explores political and social issues, Matthews refrained from public campaigning for Presidential candidates until 2004. He cast his support strongly with Democratic nominee John Kerry, performing at political events including the Vote for Change tour.

Matthews also supported Barack Obama for President in 2008, both in the primaries and in the general election.[43] On April 6, 2008, he and Tim Reynolds played a concert titled "Change Rocks"[44] at Indiana University to encourage students to register to vote. The tickets were distributed by the Obama campaign.[45] Questions regarding his citizenship were answered by advertisements and videos on YouTube, where he says he is a "real American" and a "real Virginian," stating that "real Virginians get out and vote."[46] Even though he was recently bereaved by the loss of band co-founder and saxophonist, LeRoi Moore on August 19, 2008, he and Tim Reynolds played for the Democratic National Convention delegates on Sunday, August 24 at Red Rocks,[47] and again with Reynolds at the Virginia Commonwealth University, on October 26, 2008,[48] among other places. Matthews has often supported environmental initiatives, such as biofuel availability and the fight against global climate change.[citation needed]

On September 21, 2009, Matthews stated that some of President Barack Obama's harsher critics were motivated by his race, and stated that he "sees it [racism] everywhere" in the United States.[49] Matthews is also a strong supporter of gay rights and participated in "Love Unites Shepard Fairey Equality Project", a gay marriage advocacy project.[50]

On May 10, 2012, Matthews entertained a sellout crowd at the Paramount Theatre in Seattle, Washington, where President Obama was hosting a campaign fundraiser.[citation needed]

In a September 28, 2015 interview with Rolling Stone, Matthews said that "when I hear someone like Bernie Sanders talking, I think there's a hope."[51] Matthews performed at a San Francisco rally for Sanders during the 2016 presidential primaries[52] and later, during the general election campaign, performed at a Denver rally with Hillary Clinton's vice presidential candidate, Tim Kaine[53]. He is a major donor to the 2017 gubernatorial campaign of progressive Charlottesville politician Tom Perriello.[54]

^"Blue Man FAQs". Blue Man Productions. Archived from the original on February 1, 2009. Retrieved March 6, 2009. "Sing Along," a track from The Complex, featuring Dave Matthews on vocals, is Blue Man Group's first music video.